Dog Boarding Windham
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 242 pet parents in Windham have booked dog boarding
Windham, Find top rated dog boarding
“Frankenstein and Nova spent 2days / 1 night at Bob's. They felt comfortable in the home right away, and were well taken care of. We will definitely leave the pups again.”
“Deanne was great! My husband and I both felt like we were in good hands. We loved the photo updates that she sent — we could see that our dog was happy and well cared for. Will use her services again!”
“Our dogs had a great time at Jane’s! Her home is cozy and clean and her outdoor yards are completely secure. My dogs had such a nice weekend with her that when I came to pick them up, one ran back into her house and tried to stay! Great communication and lots of photos, and she happily gave our pups their meds and made sure they were happy and comfortable. We will definitely use her again.”
“Jennifer, Thomas and their girls took such good care of our pup. They sent frequent updates and photos throughout the visit, and we could instantly tell how comfortable our dog was in their home. Cannot recommend them enough!”
“Absolutely amazing caretakers. They watched both my dogs, kept them happy, healthy, and entertained. They were able to pick up and drop off from my house, and provided photos and check ups all the time. Will definitely be using them again”
“I was beyond satisfied with my experience boarding with Aaron and Sarah. Aaron was so nice and made us feel comfortable leaving our baby with him. Will definitely book again!”
“This was our puppy's first night away and Nicole was amazing! She took such great care of our 5lb Pomeranian puppy. I received updates regularly. She has plenty of fenced in outside space and even a smaller yard for smaller dogs. Her attention to detail put my mind at ease! Highly recommend.”
“My nala girl had the BEST time! Lauren provided pictures daily and updated me everyday about her. When I picked her up she was happy, tired, and clearly had a lot of fun playing on Lauren’s ranch. I had a bit of a flight delay and Lauren was super understanding of my being a little late to pick her up so that’s also a huge plus for me. I will certainly be booking my nala girls ‘vacations’ with Lauren again!”
“Kayte was amazing!!! My dog has anxiety, but he felt right at home with Kayte. They even went on a 5-mile walk that I’ll now have to live up to haha. She sent pics daily and Onyx always looked so happy and safe. I’ll definitely be using Kayte again!!!”
“Sophia was lovely! We felt very comfortable leaving Bernie with her, and confident that she was in good hands. Sophia gave frequent updates, was easy to communicate with, and helpful throughout the planning and drop-off/pickup. Bernie had a fabulous vaycay, thank you!!!”
“🌟🌟🌟🌟🌟 While we were away in Cooperstown watching our boys play baseball, Rover made sure our pup was having just as much fun as we were! We received tons of photo updates—she always looked so happy, playing with the other dogs in a beautiful, spacious setting. It was clear she was well cared for and loved every minute. Knowing she was safe and enjoying herself gave us complete peace of mind. Highly recommend!”
“Garrett & Deanne were really great! Ruby seemed to have a great time with them. They kept me updated on how she was doing (especially with the fireworks over July 4th). I'll definitely be having them watch my girl in the future!”
“We had a family medical issue and was able to book Jacqueline quickly. Our dogs are both rescues and it matters a great deal to us who we bring into their lives. Jacqueline immediately made us, and our dogs, feel comfortable and within 5 minutes of being with them, our eldest was resting in her lap. Jaqueline sent constant photos and updates and we are very grateful to have found her and will for sure book her again. TY again, Jaqueline. That last note was from the pups!”
“This is Tyson's second time staying with Amanda. She is really good with him. She has a fenced in yard and often has multiple dogs to keep company with including her husky. Her dad even came by to see Tyson. When traveling it's such a blessing to have good people to watch your pet so you don't have to worry. I feel like he's having a sleepover at a friend's house. Thank you Amanda!”
“Sean was so great with our dog. He proactively messaged us each day and gave us updates on how our dog was doing. Our dog came back well rested and happy. We will definitely be using him again!”
“Simon watched our little pup while we went away for the weekend. The two of them became fast buddies and we were grateful to know our little guy was with someone he was so comfortable with.”
“We left our dog Luna in Jessica’s home for the first time for 2 nights and she was very well taken care of. She got a couple of walks a day and we got updates and pictures throughout the day. Jessica was very responsive to Luna’s needs and our care instructions. We wouldn’t hesitate to book with her again.”
About: I have years of experience with many different types of dogs. I watch dogs on a regular basis. For younger dogs I can offer a mountain hikes and for older dogs I can walk them on boardwalk trails that are easy on the joints, yet give the dog the sense of walking in the woods. I don't mind larger dogs at all. I also am willing to cook food for dogs. I very much enjoy the company of dogs and find that when they are well fed and exercised they are really pleasant to be around. Please give me honest description of your dog so I can plan His/Her visit accordingly. My house is set back (1000 feet) from a country road . I can pick up dogs in NYC , Great Barrington , Hudson, or Albany for a fee. I have watched many dogs over the years. Usually I try to walk them as much as possible. I feed them well , but make them follow the sit command before being fed and multiple times a day. All dogs have to be on a slip proof leash when outside or dropped off. Dogs often don't behave as they do at home . Once off a leash it can be very difficult to recapture a dog. In the house I don't crate dogs . We can only watch a few dogs at once. If your dog is very difficult let me know in advanced. Also Corgies get 10% off.
The median cost per night for dog boarding in Windham is $65
Dog parents share their Rover experiences - Windham
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
Why Choose Rover?
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Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
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We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local sitters who will treat your dogs like family
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Popular requests near you
Select a filter and find qualifying Windham sitters!Sitters in Windham average 12 repeat dog boarding clients
FAQs for Boarding - Windham
Frequently asked questions about Rover
The average cost for Dog Boarding in Windham on Rover is $37.45 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Boarding easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Boarding. For more information on service fees, click here .
As of July 2026, there are 115 sitters on Rover offering Dog Boarding across Windham. Enter your ZIP code to see which available sitters are closest to your home.
Every sitter on Rover has their own rhythm and routine, but most will follow the flow that keeps your dog happiest. Sitters can give meals on your dog's regular schedule, provide a comfortable place for sleep, and plenty of one-on-one attention.
100% of Windham sitters also include daily walks in the neighborhood during dog boarding stays. You can also request photo and message updates throughout the stay so you can see which Windham landmarks or neighborhoods your dog is enjoying.
If your dog is a little shy, consider booking a one-night trial stay! This practice run can boost your and your dog’s confidence before your trip.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Windham home-away-from-home, we recommend packing:
- Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
- Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
- Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Windham.
Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.
You and your Windham sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.
Many sitters in NY ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
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